COLLOID AND NANOSIZED CATALYSTS IN ORGANIC SYNTHESIS: XIX.
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conditional residence time of the reactants
(36.3), 81.0 (81.8), 67.1 (99.9), 41.0 (32.1). Yield of
0.00158 h kg(kt)/mol. Yield of cyclohexane 2 94%.
cyclododecane 9 50%.
Hydrogenation of 1,5-cyclooctadiene (3). a. Catalyst
Ni0/Ceokar-2 loading 7 g; 160°C; hydrogen:alkene
molar ratio 3 : 1; consumption of the reactants: alkene
0.0294 mol/h, hydrogen 0.0882 mol/h; conditional
residence time of the reactants 0.00183 h kg(kt)/mol.
Yield of cyclooctene 4 98%. Mass spectrum, m/e
(Irel,%): 109.6 (7.6) [M]+, 95.0 (15.7), 81.8 (25.1), 67.9
(10.7), 53.9 (13.0).
b. Catalyst Ni0/Al2O3 loading 7 g, 160°C, hydro-
gen : alkene molar ratio 3 : 1, consumption of the reac-
tants: alkene 0.0294 mol/h, hydrogen 0.0882 mol/h;
conditional residence time of the reactants
0.000183 h kg(kt)/mol. Yield of cyclooctane 5 16%,
yield of cyclooctene 4 76%.
e. Catalyst Ni0/NaX Zeolite loading 7 g; 240°C;
hydrogen : alkene molar ratio 5 : 1; consumption of the
reactants: alkene 0.01 mol/h, hydrogen 0.05 mol/h;
conditional residence time of the reactants
0.00302 h kg(kt)/mol. Yield of cyclododecane 9 96%.
f. Catalyst Ni0/Сact loading 2 g; 240°C; hydrogen :
alkene molar ratio 3 : 1; consumption of the reactants:
alkene 0.01 mol/h, hydrogen 0.03 mol/h; conditional
residence time of the reactants 0.00130 h kg(kt)/mol.
Yield of cyclododecane 9 96%.
Hydrogenation of dicyclopentadiene (10). a.
Catalyst Ni0/Ceokar-2 loading 7 g; 200°C; hydrogen :
alkene molar ratio 4 : 1; consumption of the reactants:
alkene 0.027 mol/h, hydrogen 0.108 mol/h; conditional
residence time of the reactants 0.00146 h kg(kt)/mol.
Yield of endo-tetrahydrodicyclopentadiene 12 91%.
Mass spectrum, m/e (Irel,%): 136.9 (3.4) [M]+, 136
(30.9), 120.9 (45.9), 95.0 (66.6), 67.0 (99.9).
c. Catalyst Ni0/NaX zeolite loading 7 g, 160°C,
hydrogen : alkene molar ratio 3 : 1, consumption of the
reactants: alkene 0.0309 mol/h, hydrogen 0.1236 mol/h;
conditional residence time of the reactants
0.0024 h kg(kt)/mol. Yield of cyclooctane 5 94%.
b. Catalyst Ni0/Al2O3 loading 7 g; 200°C; hydro-
gen : alkene molar ratio 4 : 1; consumption of the
reactants: alkene 0.027 mol/h, hydrogen 0.108 mol/h;
conditioned residence time of the reactants
0.00146 h kg(kt)/mol. Yield of 5,6-dihydrodicyclo-
Hydrogenation of trans,trans,cis-1,5,9-cyclodo-
decatriene (6). a. Catalyst Ni0/Ceokar-2 loading 7 g;
240°C; hydrogen : alkene molar ratio 3 : 1; consumption
of the reactants: alkene 0.01 mol/h, hydrogen
0.03 mol/h; conditional residence time of the reactants
0.00454 h kg(kt)/mol. Yield of cyclododecane 9 99%.
1H NMR, δ, ppm: 1.278–1.353 m (2H, CH2).
b. Catalyst Ni0/Al2O3 loading 7 g; 240°C; hydro-
gen : alkene molar ratio 3 : 1, consumption of the
reactants: alkene 0.01 mol/h, hydrogen 0.03 mol/h;
conditional residence time of the reactants
0.00454 h kg(kt)/mol. Yield of cyclododecene 26%.
Mass spectrum, m/e (Irel, %): 166.8 (1.4) [M]+, 165.8
(10.6), 108.9 (16.8), 95.0 (36.3), 81.0 (81.8), 67.1
(99.9), 41.0 (32.1). Yield of cyclododecane 9 71%.
1
pentadiene 16%. H NMR, δ ppm: 1.11–1.23 m (4H,
2СН2), 1.35 q (2H, СН2, J = 22.3 Hz), 2.03–2.18 m
(4H, СН2, 2СН), 2.42 m (1H, СН), 2.89 m (1H, СН),
5.41 m (1H, СН=), 5.51 m (1H, СН=). Yield of endo-
tetrahydrodicyclopentadiene 12 71%.
c. Catalyst Ni0/Al2O3 loading 7 g; 200°C; hyd-
rogen : alkene molar ratio 6 : 1; consumption of the
reactants: alkene 0.027 mol/h, hydrogen 0.162 mol/h;
conditional residence time of the reactants
0.00104 h kg(kt)/mol. Yield of endo-tetrahydro-
dicyclopentadiene 12 93%.
c. Catalyst Ni0/Al2O3 loading 7 g; 240°C; hydro-
gen : alkene molar ratio 5 : 1; consumption of the
reactants: alkene 0.01 mol/h, hydrogen 0.05 mol/h;
conditional residence time of the reactants
0.00302 h kg(kt)/mol. Yield of cyclododecane 9 95%.
d. Catalyst Ni0/NaX Zeolite 7 g, 240°C, hydrogen :
alkene molar ratio 3 : 1, consumption of the reactants:
alkene 0.01 mol/h, hydrogen 0.03 mol/h; conditional
residence time of the reactants 0.00454 h kg (kt)/mol.
Yield of cyclododecene 37%. Mass spectrum, m/e (Irel,
%): 166.8 (1.4) [M]+, 165.8 (10.6), 108.9 (16.8), 95.0
d. Catalyst Ni0/NaX zeolite loading 7 g; 200° C;
hydrogen : alkene molar ratio 4 : 1; consumption of the
reactants: alkene 0.027 mol/h, hydrogen 0.108 mol/h;
conditional residence time of the reactants
0.00146 h kg(kt)/mol. Yield of endo-tetrahydrodi-
cyclopentadiene 12 90%.
e. Catalyst Ni0/Сact loading 2 g; 200°C; hydrogen :
alkene molar ratio 4 : 1, consumption of the reactants:
alkene 0.027 mol/h, hydrogen 0.108 mol/h; conditional
residence time of the reactants 0.00042 h kg(kt)/mol.
Yield of endo-tetrahydrodicyclopentadiene 12 93%.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 88 No. 1 2018